One way or another, the World Series will be over by next week, and free agency will begin five days after the final out.
The Boston Red Sox have plenty on their to-do list this winter, including adding to the rotation.
We sent out the call for mailbag questions, and readers sent in plenty. We’ll dig into part two here with an emphasis on potential trades for the rotation, Jarren Duran’s future, prospects on the trade block and more.
If you missed part one on Thursday, we dug into how Pete Alonso and Kyle Schwarber could fit the lineup, what a pair of Japanese free agent hitters could bring, Triston Casas’ future and other burning questions.
With our outfield and prospect depth, which starter is most realistic as a No. 2 addition (by trade) to accompany Garrett Crochet in the rotation? Sandy Alcantara (one year remaining at $17M), Joe Ryan (not a proven No. 2), Tarik Skubal (Scott Boras client). I don’t like the free-agent starter options this year? – David G
I think a good starting point for what the Red Sox are willing to trade for a top starter is to look back at the Crochet deal with the Chicago White Sox.
It was chief baseball officer Craig Breslow’s first major trade and a pretty bold one at that. At the time of the December deal, Crochet was 25 years old with two years of control left, and the Red Sox gave up two top-50 prospects in 2023 first-round catcher Kyle Teel and 2024 first-round outfielder Braden Montgomery. They also traded two mid-tier prospects in Triple-A infielder Chase Meidroth and right-hander Wikelman Gonzalez. Every trade partner is different and has different needs, but that’s what the Red Sox were willing to give up for a young ace.
Let’s start with Skubal. The reigning American League Cy Young winner, who’s likely to win the award again this year, would not be a No. 2 behind Crochet. It would be more of a 1 and 1A between the starters, though Skubal’s hardware gives him an edge. Either way, Skubal would cost a lot.
In checking in with The Athletic’s Tigers writer Cody Stavenhagen, the Tigers likely would want a major-league-ready starting pitcher and hitter, preferably a right-handed hitting shortstop or center fielder.
A deal for Skubal most likely starts with Payton Tolle or Connelly Early, in addition to a top young hitter or two. Roman Anthony is all but off the table. The Tigers might want Marcelo Mayer (even as a lefty hitter), but it seems more likely the Red Sox would offer Double-A shortstop Franklin Arias or Triple-A outfielder Jhostynxon Garcia, both top 50 in baseball and top 10 prospects in the Red Sox system.
The Tigers may also be interested in Jarren Duran (despite being another lefty), given he’s a proven big leaguer, despite a less productive season compared to his breakout 2024. That he’s under control through 2028 is a key piece for a Tigers team looking to compete.
A deal for Skubal is tricky to predict because he is perhaps the best pitcher in baseball at the moment, but has just one year of control left and is turning 29 this month. Moreover, as a Scott Boras client, many predict that if he’s traded this winter, he wouldn’t sign an extension with his new team, preferring to enter free agency next winter, when he could fetch $400 million. However, a potential MLB lockout does complicate that scenario a bit. Regardless, I think a Skubal trade at the least starts with Tolle and/or Early, Duran and possibly Garcia or Arias. The Red Sox would have to be fairly confident they can sign Skubal to an extension if they gave up that kind of haul.
We’ll move to Joe Ryan next. The Red Sox were in pursuit of Ryan at the deadline, but talks fell apart. As a reminder, the right-hander is 29 and under control through 2027. He’s not as elite as Skubal, but would be a solid No. 2 behind Crochet. Dan Hayes, The Athletic’s Twins writer, suggested Minnesota would be seeking two top-50 prospects, one with a mid-ceiling and one more of a lottery ticket.
In this scenario, Garcia projects as a solid everyday, mid-ceiling center fielder with power, an area of surplus for the Red Sox. The Twins don’t particularly need outfielders, though. Arias, currently ranked as the top Red Sox prospect and No. 9 in baseball by The Athletic’s Keith Law, projects as an everyday shortstop with plenty of upside and could be a fit, though the Twins’ middle infield is solid.
Boston’s 2025 first-rounder, right-hander Kyson Witherspoon, landed among Law’s top-60 prospects after the draft last season, and if the Twins want pitching in return, the Red Sox might be more inclined to trade Witherspoon as opposed to Tolle or Early. Arias or Garcia, along with Witherspoon, could be a good start for a deal with Ryan.
Sandy Alcantara isn’t pitching at the same level as a Tarik Skubal, but almost nobody else is either. (Matthew Stockman / Getty Images)
Lastly, we’ll look at Alcantara. The 30-year-old right-hander has one year, $17 million left on a five-year, $56 million deal he signed in 2022. That deal does have a team option of $21 million for 2027. Alcantara won a Cy Young award in 2022, but missed the 2024 season with Tommy John surgery. He proved healthy this past season in his return, making 31 starts. Though he posted a 5.36 ERA on the season, he found his rhythm in the second half with a 3.33 ERA over his final 13 starts compared to a 7.22 ERA in his first 18 starts after returning. Even with the uncertainties and age, Alcantara’s second half seemed to quiet some of the questions surrounding his return. Meanwhile, his contract makes him extremely affordable for a very good pitcher, and because of that, the Marlins have leverage, even if he’s not at the level of Ryan or Skubal.
The Yankees reportedly weren’t willing to part with two of their top position player prospects in Spencer Jones or George Lombard Jr. for Alcantara at the deadline this summer, but a Red Sox package of Garcia along with Witherspoon or left-hander Brandon Clarke, a top 10 pitcher in the system, and Kristian Campbell could entice the Marlins, who are always seeking to add controllable players.
Breslow pulled off the Crochet trade to add to the rotation last winter, and the Red Sox seem to have enough in their farm system to add another big arm. With the free-agent pitcher class led by Framber Valdez, Dylan Cease and Ranger Suarez, all 30 or older and likely to fetch six-year deals worth more than $175 million, the Red Sox may get more bang for their buck on the trade market.
What are the odds that both Early and Tolle are in the rotation to start the ’26 season? – Jack F
Ideally, the Red Sox would like them both to start in Triple A for a bit more development. They each held their own in the majors in intense, meaningful games late in the year and into the postseason, but that doesn’t mean there’s zero room for improvement. Tolle needs to work on refining his secondaries so he doesn’t get exposed as hitters catch up to his elite fastball. Early has to work on holding his velocity and further developing his slider and curveball.
That said, I think Early is a bit ahead of Tolle, both in development because he’s a year further along and in terms of his major league readiness. I could see a scenario where he’s the No. 5 starter on Opening Day, but of course, there are a lot of moving parts this winter. We’ve also seen that the rotation the team thinks it has at the start of spring inevitably gets shuffled because of a pitcher injury or setback in the spring.
Is there any chance that Jarren Duran, with a full offseason and spring training to prepare, could shift to second base? This would alleviate the outfield logjam and plug the hole at second. – Derrick E
We got a few questions about this possibility, but to my knowledge, it’s not something the Red Sox are considering. Duran came up through the minors as a second baseman, and in theory, it makes sense as a solution to the team’s problems. But given he’s never taken infield reps in the majors, I think it could worsen the team’s infield defense rather than help.
Duran was a Gold Glove finalist in center in 2024, but shifted to left to make room for Ceddanne Rafaela in center. Despite negative-4 Outs Above Average in left this year, Duran still managed 9 Defensive Runs Saved and tallied 10 outfield assists, fifth in the majors and ahead of Rafaela’s eight assists. In my mind, it’s more likely that Duran gets traded than moved to second base.
While on the topic of Duran, the Red Sox do have a contract decision for him looming after the World Series. Last offseason, Duran and the Red Sox could not come to terms initially on an arbitration deal when the deadline passed. Duran wanted $4 million; the Red Sox offered $3.5 million. Before the sides headed to an arbitrator, they settled on a one-year, $3.85 million deal with a team option of $8 million for 2026. The Red Sox need to decide whether to pick up that $8 million option next week.
MLBTradeRumors.com projects Duran making $8.4 million in arbitration if the option is declined, so the Red Sox may decide to pick up the option rather than head back to arbitration. Arbitration can be a tenuous process with the team basically telling the player how much they think he’s worth. Even in picking up the $8 million option, they could still trade Duran, who is 29 and under control through 2028. How they approach that deal next week will be something to watch.
Considering the status of the kids on the farm with the Sox organization, which three or four guys look like they’re on the fast track to the majors? – Elaine A.
Among the likeliest to contribute in the majors this season is right-hander Luis Perales, whom we wrote about last week. Though he’s working his way back from 2024 Tommy John surgery, he’s flashed the same 100 mph fastball in the Arizona Fall League this year that he displayed before his injury. Working on regaining command is his focus this fall and into the spring. If he continues to do that in camp and into the early part of the year at Triple A, he could be an early-to-midseason call-up for a depth starter or multiple innings in the bullpen if needed.
Infielder Mikey Romero has dealt with his fair share of injuries since being drafted in the first round in 2022, but he is getting closer to a debut. In 111 games between Double A and Triple A last season, he hit .245 with a .721 OPS and could be a utility player who gets a call midseason.
Right-hander Tyler Uberstine is another pitcher who could debut next year, likely as a multi-inning reliever or spot starter a la Cooper Criswell. He posted a 3.58 ERA in 25 games, 21 starts, for Double A and Triple A last year.
